Season Break Nugget 1: Pick Your Two Favorites
We’re on a quick hiatus before Season 2, premiering Oct 7, but that doesn’t mean the show stops! We’re back this week with bonus nuggets as we gear up for the new season. You’ll hear all about Chelsea...
23 Sep 202119min
Coming Soon: Dear Chelsea Season 2!
Hey fans, just a reminder that we are on a quick hiatus before Season 2, premiering Oct 7. Watch this space! Starting next Thursday, we’ll be dropping some bonus minisodes as we gear up for the new se...
16 Sep 202153s
Confidence or Confidant?
In the season finale, Chelsea and Brandon discuss Chelsea’s new tour and why you should sleep with your roommates while you’re in your 20’s. A Latina filmmaker loses her confidence now that she’s in a...
9 Sep 202145min
Hitting On People At Funerals
Chelsea and Brandon tackle the age-old question: should you try to hook up with your childhood crush at their mother’s funeral? A teacher chooses between working with her best friend or landing a bett...
2 Sep 202146min
No-No Square
Chelsea and Brandon discuss the trouble with teenagers, the horrors of minivan transportation, and why turndown service might not be so great after all. A Melbourne mom-to-be begs for help as childbir...
26 Aug 20211h
Our Worst Advice Yet
An ex-Mormon has trouble making a romantic connection, even though he dates both men and women. A law student feels the pressure of losing a year to Covid, and debates whether to focus on her educatio...
19 Aug 202154min
Time to Give Your Family the Boot
A girlfriend wants to know if her boyfriend’s second DUI is a relationship dealbreaker. A 21-year-old wonders if marriage is the solution after feeling judged about her live-in partner. And a couple...
12 Aug 20211h 8min
Sextuple Threat
Chelsea and Brandon discuss what Chelsea is like on a movie set, and why you should never date your ex’s sibling. A bookkeeper from Milwaukee wants to get rich quick as an influencer. A girlfriend is ...
5 Aug 202138min
